


I Double Triple Dog Dare You

by DarkStarfish



Category: Shall We Date?: Obey Me!
Genre: Anal Plug, Breeding, Breeding Kink, Butt Plugs, Clothed Sex, Creampie, Crossdressing, Crossdressing Kink, Daddy Kink, Dubious Consent, Gratuitous Smut, Lingerie, M/M, Mating Press, Plot What Plot/Porn Without Plot, Praise Kink, Sex Toys, Sex Toys Under Clothing, Shameless Smut, Size Kink, Smut, Thighs, Throne Sex
Language: English
Status: Completed
Published: 2020-09-27
Updated: 2020-09-27
Packaged: 2021-03-06 21:47:52
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,642
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26462158
Author URL: https://archiveofourown.org/users/DarkStarfish/pseuds/DarkStarfish
Summary: Another request for the lovely astrablossom!Levi gets dared by Asmo to seduce Diavolo and thing go well...a little too well if you ask Levi...In case you were interested or wanted a better idea of the lingerie set I picked, I chose this (https://images.app.goo.gl/j2KGTMyjQBrV7kWJ9) beautiful look as my reference picture and added a few details on top of it ^^
Relationships: Diavolo/Leviathan (Shall We Date?: Obey Me!)
Comments: 8
Kudos: 152





	I Double Triple Dog Dare You

**Author's Note:**

  * For [velnoni](https://archiveofourown.org/users/velnoni/gifts).



Levi had no idea what prompted Asmo to bust into his room unannounced but given his current situation, he wished his brother would have just kept to himself. Asmo had interrupted his usual gaming marathon, his sickly-sweet voice pulling Levi out of the immersive experience of the RPG he’d just gotten from Azukon. When Levi had taken off his headset, he was sent into a blushing fit. Asmo was carrying lingerie, and, by the looks of it, it was expensive lingerie.

“I have a little challenge for you big brother,” Asmo cooed out, his hands stroking the feather detail on the elaborate mesh robe that went with the ensemble.

“Whatever it is, challenge declined,” Levi huffed, swiveling in his chair so he was back to facing his computer.

“Oh? Not even if it means I’ll give you the limited edition Ruri-chan figure you missed out on last month?”

Asmo had Levi’s attention. The third born swiveled back in his chair to face Asmo, his hands coming up to move his headphones around his neck so he could hear his brother better. Based on the smug look on his face, Levi could tell it was a trap, but if Asmo was talking about THE Ruri-chan figure, then there was no way Levi could say no.

“Do you mean the–”

“The alternately colored beach figure with exchangeable body preorder that they only made one hundred of? Yes that one,” Asmo cooed evilly. He’d flashed his pearly white smile to Levi, knowing that he had his brother right where he wanted him.

“How did you even get that?! I stayed up three days straight to try and get it when it dropped!” Levi was out of his gaming chair then, outraged that a normie like Asmo got the upper hand on him.

“I have my sources…are you going to hear me out or are we going to stand here all day? I’ll be late for my mani pedi,” Asmo huffed, looking at his nails longingly.

“Just get on with it,” Levi mumbled out, his words muffled by his palm pressed against his face in even further embarrassment.

“Fabulous!” Asmo moved further into Levi’s room, cringing at the way the multicolored LED lights of his older brother’s room made his skin look. He’s draped the lingerie he was carrying over Levi’s peculiar choice of a bed and smoothed out the silk fabric lovingly.

“So about this ‘little’ challenge…” Asmo started, a mischievous little giggle lacing his words as he spoke. “I double triple dog dare you to seduce our favorite demon prince, Lord Diavolo, and if it goes well, then that hunk of plastic is yours.”

“Okay, first of all, don’t ever refer to Ruri-chan as a ‘hunk of plastic’ and second, WHY DIAVOLO?!” Levi squawked, his arms flailing wildly. He knew Asmo was creative when it came to getting his way but putting such a precious figure on the line was a new low, even for the lustful demon.

“Well I mean if you’re not interested…”

Asmo had turned on his heel to leave, but he’d stopped at the feeling of Levi pulling him back by his arm. The Avatar of Lust gave his older brother a wolfish grin, knowing he had his brother hooked.

<br>

It was the steps of Diavolo’s castle that Levi started to get cold feet. It was odd to him that Barbatos wasn’t at the door to greet him like he always was, but, just as Asmo said, he was nowhere in sight. While it was unnerving, Levi took it his saving grace in escaping embarrassment while dressed like…this…

Just like everything his younger brother did, there was no shortage of flashiness in the lingerie Asmo had provided. While the lingerie was black, it had little accents of red rhinestones that had been more concentrated in the breast and crotch areas of the matching bra and panties. Levi had guessed it was for modesty, but it was a silly concept to have in an article of ‘clothing’ that was made entirely of lace. The Avatar of Envy took one last look at himself before entering Diavolo’s throne room. He’d adjusted the sheer thigh high stockings and the garter around his waist that kept everything up, more so procrastinating opening the door than anything else.

Finding nothing else to fix on his outfit, Levi let out a deep sigh and gulped. His hand met the cool metal of the throne room door knob and he’d turned it without another thought. Levi’s black stiletto heels clicked on the tile flooring, the sound echoing through the quiet room, easily catching Diavolo’s attention. The demon prince looked up from one of the many proposals for RAD clubs, fully prepared to greet whoever it was that decided to drop in with his usual cheerful smile. Said smile faltered at the sight of Levi and his choice of dress, a lump forming in the royal’s throat as he took in the sight before him.

Levi blushed at Diavolo’s staring, one of his hands coming up to cover his mouth as he looked away from the royal. The pair were relatively silent as they both mulled over what exactly to say about the current situation. It wasn’t like Levi to do something so bold and it certainly wasn’t like Diavolo to be so quiet.

“To what do I uhh…owe the pleasure?” Diavolo spoke quietly, his voice shaky as he tried to keep his tone even. He hadn’t wanted to frighten Levi off, hoping to find out why exactly the Avatar of Envy decided to drop by unannounced and in lingerie no less.

Levi didn’t respond at first. He’d mapped out scenario after scenario in his mind of what to say and none of them seemed to work out perfectly. He had no idea how to be sexy and sure as hell didn’t know how to seduce anyone. With his beloved Ruri-chan on the line, Levi made up his mind to just suck it up and do his best. Levi straightened his posture, the lace robe from the lingerie falling to hang off his elbows as he squared his shoulders and stood proud.

“I just thought you might want a little company my Lord. Cooped up in this castle all by yourself…” Levi cooed out, his heels clicking once more as he approached Diavolo up on his throne. “Working so hard…maybe a reward is in order?”

Diavolo watched Levi like a hawk as the demon approached him, his golden eyes taking in every bit of creamy white skin that was exposed by the lingerie set. The Prince jumped in his skin at bit when he felt the teasing of Levi’s fingertips on his arm. He hadn’t realized the Avatar of Envy had gotten so close and Diavolo felt his throat tighten a bit as he tried to keep himself under control. 

“Ahem…well this is very…” Diavolo trailed off, trying to find the right word for it.

“Unexpected? Well surprises can be nice don’t you think…?” Levi tried, hoping that he wasn’t losing Diavolo by being so forward. 

“Well yes, but it’s not something I would expect from you Levi.” Diavolo shrugged then, worried that maybe Levi was just messing with him.

“I’m here now aren’t I?” Levi challenged, an eyebrow quirking. He’d hoped Diavolo was taking the bait, but based on the way things were going, it was unlikely that he was.

“I mean, you are but –”

“Then come unwrap your surprise daddy.”

Levi had no idea what came over him or why he even called Diavolo that, but it seemed to set the demon prince off. A deep growl sounded from Diavolo’s throat and it made a dangerous shiver run down Levi’s spine. The Avatar of Envy was ready to back out of Asmo’s little bet, but Diavolo had boxed Levi in and the royal was circling him like a tasty piece of meat on a platter. When he’d felt Diavolo’s hand push the robe from his elbows, the expensive fabric pooling at his feet, Levi knew there was no turning back now.

“Shy all of the sudden aren’t we?” Diavolo chuckled, his voice close to the back of Levi’s neck. “What happened to my little minx hmm?”

“I-I-I…ahh!”

Levi tried to speak, he really did, but Diavolo nibbling at the skin just under his ear sent a shiver down his spine. He found his words falling on the tip of his tongue whenever he’d opened his mouth and little whimpers and whines came out instead. Levi’s focus had been taken away from the sensation of Diavolo’s teeth sinking into his delicate skin to the feeling of Diavolo’s fingertips stroking at the tops of his thighs where the stockings ended, the skin there a bit pillowy from just how tight the sheer material was on him. 

“You’re so soft pet…” Diavolo hummed, his tongue tracing over the little scales on the side of Levi’s neck as he spoke. At the feeling of Levi’s tail curling around his leg, Diavolo chuckled, the sound rich and deep in Levi’s ear. 

Diavolo’s fingertips traced higher as he continued to tease at the skin and scales of Levi’s neck, the demon in his grasp squirming and whimpering with each flick of his tongue. The demon prince traced the silk fabric of the garter straps holding up Levi’s stockings until he reached the lace panties the demon was wearing. His fingertips traced at the trim, barely touching Levi as he traced up to the waistband. Diavolo just barely dipped his fingers under the elastic, teasing the sea demon even further. With a sly grin, Diavolo removed his hand completely, growling at the little whine of disappointment Levi made.

“Don’t worry pet, I’ve got something special in mind for you…”

Diavolo completely left Levi then. The Avatar of Envy whined at the loss of the royal’s teasing. Levi’s skin was blushed a soft pink color from both Diavolo’s teasing and his own arousal creeping up on him. Levi could feel Diavolo’s presence behind him still and the archdemon waited for the larger demon to do something and as it turned out, Levi didn’t have to wait too long. Diavolo had pulled Levi’s panties to the side and gasped at what he saw.

“H-hey! W-wait!” Levi squawked, his body trembling in embarrassment. He knew what Diavolo found and Levi wasn’t particularly proud of what the royal discovered. 

“Fuck…I never thought my little pet would be such an eager little whore…” Diavolo growled, his eyes trained to the plug in Levi’s ass, the toy ensuring Levi was prepped and ready for him. 

Diavolo tried to keep himself under control but seeing the plug had been the nail in the coffin. The demon prince snapped. Impatiently, Diavolo swooped Levi up princess style to carry Levi to his throne. Diavolo unceremoniously dropped Levi into the seat of the throne, the demon’s back in the corner of the chair, leaving him in an uncomfortable position. Levi opened his mouth to protest, but any words his mind planned out quickly became lost at the feeling of Diavolo nudging the plug in his ass, the tip of it brushing against his prostate.

The sight below Diavolo drove him crazy. The future king of the Devildom tracked every one of Levi’s movements, from the back of his hand covering his face as he blushed to the twitching of Levi’s dual cocks that were barely being held back the panties he was wearing. Diavolo fumbled with his buckle and his zipper, his tongue swiping across his bottom lip as he watched a little patch appear on the lace fabric of the panties Levi was wearing, allowing for Diavolo to get a little peak the angry red tip of Levi’s cocks. 

Diavolo let out a relieved sigh once his erection was free from its cloth prison, giving the length of it a few jerks as he continued to play with the toy in Levi’s ass. At a particularly breathy moan from Levi, Diavolo lost the last bit of self-control he had. With a rumbling groan, Diavolo tugged at the plug in Levi’s asshole. The smaller demon’s breath hitched at the plug being pulled from him, a needy whimper leaving him once the toy was out of him and he felt the broad tip of Diavolo’s cock nudging at his entrance.

A surprised gasp bubbled up from Levi’s throat when he felt the expanse of Diavolo’s hands at the back of his thighs, the demon prince pressing the third born’s knees up to his chest. The sounds of their combined panting and the clattering of one of Levi’s heels falling off his foot filled the room. Diavolo hesitated for a moment, concerned for Levi’s posture, but he was immediately set off by Levi’s pleas.

“Daddy…! Please!” Levi hiccupped and his cries were soon satisfied by Diavolo pushing his cock into Levi’s slick entrance. 

Diavolo quickly set a brutal pace, his hips slamming into Levi’s as he went. Levi’s body jerked and contorted with every push of Diavolo’s hips, his lips permanently parted so moans could freely flow from them. Each pass of Diavolo’s cock cause the mushroom head of it to brush at Levi’s prostate, his cock jumping and leaking from every little nudge at the spot. Diavolo huffed and growled with every thrust, his nails digging into the soft plush of Levi’s thighs as he tried to ground himself. 

“You feel so fucking good pet…” Diavolo punctuated each of his words with a deep thrust, his hips bones meeting Levi’s to ensure he was going balls deep each time. 

In the middle of one of his thrusts, Diavolo faltered, his hips stuttering. He felt Levi’s tail nudge at his asshole, the tip of it barely dipping into his entrance. It made him chuckle, the sound rich in Levi’s ears and the Avatar of Envy found himself caught off guard by Diavolo pushing back into the sensation. As quickly as Diavolo paused, the demon prince resumed his powerful thrusting.

“Nnng…close!” Levi gasped out, the huge wet spot in his panties from where his cocks were leaking precum evidence enough of his impending orgasm. 

“Me too pet…fuck…’m gonna fill you up…” Diavolo’s words took on a whiney quality to them as his own orgasm approached, his cock throbbing wildly in Levi’s tight hole.

“Unng! Yes daddy…please breed me…wannafeelyoucuminmepleaseplease!!”

Levi’s blabbering pushed them both over the edge. Diavolo pushed his hips forward one last time, cumming into Levi with deep growl. The thick feeling of Diavolo’s cum filling him up sending Levi over the edge. Levi shot rope after rope of his cum into the panties he was wearing, the lace fabric sticking uncomfortably to his throbbing lengths. Diavolo stayed seated inside Levi’s abused hole as the two came down, his hips nudging into Levi’s to make the demon whimper from overstimulation. 

“You did so well pet…” Diavolo sighed out, pulling his hips back slightly.

Diavolo angled Levi’s hips up once he’d pulled his softened cock from Levi’s hole, ensuring none of his seed would be wasted. He’d grabbed the plug Levi had inside him and gently pushed it into the demon. Levi’s breath hitched at the even fuller feeling of Diavolo’s cum and the plug filling him up. The demon prince stared down at the mess below him, smiling smugly at how wrecked Levi looked. 

“You’ve been so good for me pet…now keep this in here until I can fill you up some more…”

Levi’s eyes widened at Diavolo’s words. It seemed Asmo’s plan for Levi to seduce Diavolo worked a little too well. The Avatar of Envy cursed silently to himself and just had to remind himself that it was worth it if it meant he would have his precious Ruri-chan.

**Author's Note:**

> Join the discord if you guys want to join to get updates on fics, chat about Obey Me! or just talk in general! It also helps me keep requests in line if anyone wants to make one!
> 
> https://discord.gg/E2gzSbx  
> |  
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> 
> https://twitter.com/tweetingjulens1?s=09


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